CN1478092A - 苯并噁嗪酮衍生物及其制备和应用 - Google Patents
苯并噁嗪酮衍生物及其制备和应用 Download PDFInfo
- Publication number
- CN1478092A CN1478092A CNA018197663A CN01819766A CN1478092A CN 1478092 A CN1478092 A CN 1478092A CN A018197663 A CNA018197663 A CN A018197663A CN 01819766 A CN01819766 A CN 01819766A CN 1478092 A CN1478092 A CN 1478092A
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- CN
- China
- Prior art keywords
- methyl
- benzo
- oxygen base
- oxazine
- ketone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 238000002360 preparation method Methods 0.000 title claims description 22
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 251
- -1 C1-6alkanoyl Chemical group 0.000 claims abstract description 211
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 206
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims description 200
- 125000005936 piperidyl group Chemical group 0.000 claims description 124
- 239000000203 mixture Substances 0.000 claims description 109
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 107
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 81
- 238000013459 approach Methods 0.000 claims description 77
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 53
- 239000011734 sodium Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 22
- 125000005605 benzo group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000002541 furyl group Chemical group 0.000 claims description 17
- 125000004193 piperazinyl group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000005493 quinolyl group Chemical group 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 11
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 208000024732 dysthymic disease Diseases 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000005533 aryl carboxamido group Chemical group 0.000 abstract 1
- 125000005421 aryl sulfonamido group Chemical group 0.000 abstract 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 1
- 150000003976 azacycloalkanes Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 174
- 238000001819 mass spectrum Methods 0.000 description 109
- 239000008186 active pharmaceutical agent Substances 0.000 description 108
- 238000005481 NMR spectroscopy Methods 0.000 description 104
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 82
- 238000007738 vacuum evaporation Methods 0.000 description 79
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 76
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 76
- 239000000243 solution Substances 0.000 description 61
- 239000007787 solid Substances 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 238000003756 stirring Methods 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 239000012074 organic phase Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000007788 liquid Substances 0.000 description 30
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 26
- AETRCWQLVCVHMF-UHFFFAOYSA-N CCBr.[O] Chemical compound CCBr.[O] AETRCWQLVCVHMF-UHFFFAOYSA-N 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 24
- 238000001816 cooling Methods 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000010898 silica gel chromatography Methods 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000010828 elution Methods 0.000 description 18
- 229960001866 silicon dioxide Drugs 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000005406 washing Methods 0.000 description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 229910052786 argon Inorganic materials 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000605 extraction Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 8
- YXTROGRGRSPWKL-UHFFFAOYSA-N 1-benzoylpiperidine Chemical class C=1C=CC=CC=1C(=O)N1CCCCC1 YXTROGRGRSPWKL-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- FDLDWKIEWAWOSL-UHFFFAOYSA-N ethyl acetate;2-methylpentane Chemical compound CCCC(C)C.CCOC(C)=O FDLDWKIEWAWOSL-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- WYSPMXSNCAFCFV-UHFFFAOYSA-N methyl 2-fluoro-4-hydroxybenzoate Chemical class COC(=O)C1=CC=C(O)C=C1F WYSPMXSNCAFCFV-UHFFFAOYSA-N 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- SCDOECQNQZPWAJ-UHFFFAOYSA-N 2-methylquinolin-5-ol Chemical compound OC1=CC=CC2=NC(C)=CC=C21 SCDOECQNQZPWAJ-UHFFFAOYSA-N 0.000 description 4
- KOMTXTIVANEKOH-UHFFFAOYSA-N 7-chloro-2-methylquinolin-5-ol Chemical compound OC1=CC(Cl)=CC2=NC(C)=CC=C21 KOMTXTIVANEKOH-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- DZAHXNNEQCZPGJ-UHFFFAOYSA-N CCCCOC(OC)=O.COC(O)=O Chemical class CCCCOC(OC)=O.COC(O)=O DZAHXNNEQCZPGJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
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- GRVQXFRJNJGBPE-UHFFFAOYSA-N 8-chloro-2-methylquinolin-5-ol Chemical compound OC1=CC=C(Cl)C2=NC(C)=CC=C21 GRVQXFRJNJGBPE-UHFFFAOYSA-N 0.000 description 3
- NQLZMZUHESIKLL-UHFFFAOYSA-N 8-fluoro-2-methylquinolin-5-ol Chemical compound OC1=CC=C(F)C2=NC(C)=CC=C21 NQLZMZUHESIKLL-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 3
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- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 208000015114 central nervous system disease Diseases 0.000 description 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 3
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- 238000010790 dilution Methods 0.000 description 3
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- 238000009472 formulation Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- HPENIXPTZDLZMQ-UHFFFAOYSA-N methyl 2-(4-hydroxy-2-nitrophenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C=C1[N+]([O-])=O HPENIXPTZDLZMQ-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ZGZNHMRNYVOPNJ-UHFFFAOYSA-N 2-methylquinazolin-5-ol Chemical compound OC1=CC=CC2=NC(C)=NC=C21 ZGZNHMRNYVOPNJ-UHFFFAOYSA-N 0.000 description 2
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000004175 ponceau 4R Substances 0.000 description 1
- 235000012731 ponceau 4R Nutrition 0.000 description 1
- 235000019238 ponceau 6R Nutrition 0.000 description 1
- 235000019237 ponceau SX Nutrition 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- GYESAYHWISMZOK-UHFFFAOYSA-N quinolin-5-ol Chemical compound C1=CC=C2C(O)=CC=CC2=N1 GYESAYHWISMZOK-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- BLGXFZZNTVWLAY-DIRVCLHFSA-N rauwolscine Chemical compound C1=CC=C2C(CCN3C[C@H]4CC[C@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-DIRVCLHFSA-N 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 239000004180 red 2G Substances 0.000 description 1
- 235000012739 red 2G Nutrition 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000019234 riboflavin-5-sodium phosphate Nutrition 0.000 description 1
- 239000004248 saffron Substances 0.000 description 1
- 235000013974 saffron Nutrition 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 239000003727 serotonin 1A antagonist Substances 0.000 description 1
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 201000002859 sleep apnea Diseases 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 208000000995 spontaneous abortion Diseases 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000004173 sunset yellow FCF Substances 0.000 description 1
- 235000012751 sunset yellow FCF Nutrition 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 229940120293 vaginal suppository Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000004108 vegetable carbon Substances 0.000 description 1
- 235000012712 vegetable carbon Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 235000019235 yellow 2G Nutrition 0.000 description 1
- GQDDNDAYOVNZPG-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C[C]2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3N=C21 GQDDNDAYOVNZPG-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- 229940032912 zephiran Drugs 0.000 description 1
- 229960002791 zimeldine Drugs 0.000 description 1
- OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0026224A GB0026224D0 (en) | 2000-10-26 | 2000-10-26 | Novel compounds |
| GB0026224.6 | 2000-10-26 | ||
| GB0111858A GB0111858D0 (en) | 2001-05-15 | 2001-05-15 | Novel compounds |
| GB0111858.7 | 2001-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1478092A true CN1478092A (zh) | 2004-02-25 |
Family
ID=26245199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA018197663A Pending CN1478092A (zh) | 2000-10-26 | 2001-10-22 | 苯并噁嗪酮衍生物及其制备和应用 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6939871B2 (pt) |
| EP (1) | EP1330460B1 (pt) |
| JP (1) | JP4242643B2 (pt) |
| KR (1) | KR20030051747A (pt) |
| CN (1) | CN1478092A (pt) |
| AR (1) | AR034174A1 (pt) |
| AT (1) | ATE357448T1 (pt) |
| AU (1) | AU2002224791A1 (pt) |
| BR (1) | BR0114881A (pt) |
| CA (1) | CA2426706A1 (pt) |
| CZ (1) | CZ20031163A3 (pt) |
| DE (1) | DE60127434T2 (pt) |
| ES (1) | ES2280417T3 (pt) |
| HU (1) | HUP0301458A2 (pt) |
| IL (1) | IL155520A0 (pt) |
| MX (1) | MXPA03003820A (pt) |
| NO (1) | NO20031838L (pt) |
| PL (1) | PL366378A1 (pt) |
| TW (1) | TWI237023B (pt) |
| WO (1) | WO2002034754A2 (pt) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0203811D0 (en) | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| GB0203804D0 (en) | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| GB0203778D0 (en) * | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| GB0209244D0 (en) * | 2002-04-23 | 2002-06-05 | Glaxo Group Ltd | Compounds |
| WO2004029048A1 (en) * | 2002-09-26 | 2004-04-08 | Warner-Lambert Company Llc | Heterocyclic substituted piperazines for the treatment of schizophrenia |
| DE50312598D1 (de) | 2002-10-10 | 2010-05-20 | Morphochem Ag Komb Chemie | Neue verbindungen mit antibakterieller aktivität |
| DE60318733T2 (de) | 2002-11-08 | 2009-01-15 | F. Hoffmann-La Roche Ag | Substituierte benzoxazinones und ihre verwendung |
| GB0227240D0 (en) * | 2002-11-21 | 2002-12-31 | Glaxo Group Ltd | Compounds |
| UA82875C2 (en) * | 2003-04-30 | 2008-05-26 | Insecticidal (dihalopropenyl) phenylalkyl substituted dihydrobenzofuran and dihydrobenzopyran derivatives and method for controlling insects | |
| GB0310849D0 (en) * | 2003-05-12 | 2003-06-18 | Glaxo Group Ltd | Compounds |
| GB0310851D0 (en) * | 2003-05-12 | 2003-06-18 | Glaxo Group Ltd | Compounds |
| GB0316915D0 (en) | 2003-07-18 | 2003-08-20 | Glaxo Group Ltd | Compounds |
| CN101365696A (zh) * | 2004-07-28 | 2009-02-11 | Irm责任有限公司 | 作为类固醇激素核受体调节剂的化合物和组合物 |
| KR20080064953A (ko) * | 2005-10-13 | 2008-07-10 | 모르포켐 악티엥게셀샤프트 퓌르 콤비나토리셰 케미 | 항균 활성을 갖는 5-퀴놀린 유도체 |
| JP5662346B2 (ja) | 2009-01-21 | 2015-01-28 | バジリア ファルマスーチカ アーゲーＢａｓｉｌｅａ Ｐｈａｒｍａｃｅｕｔｉｃａ ＡＧ | 新規二環式抗生物質 |
| KR101891834B1 (ko) | 2009-12-18 | 2018-09-28 | 바실리어 파마슈티카 아게 | 트리시클릭 항생제 |
| US9321788B2 (en) | 2011-06-17 | 2016-04-26 | Basilea Pharmaceutica Ag | Tricyclic antibiotics |
| MX2018014032A (es) | 2017-03-20 | 2019-08-21 | Forma Therapeutics Inc | Composiciones de pirrolopirrol como activadores de piruvato cinasa (pkr). |
| EP3853206B1 (en) | 2018-09-19 | 2024-04-10 | Novo Nordisk Health Care AG | Treating sickle cell disease with a pyruvate kinase r activating compound |
| CN113226356A (zh) | 2018-09-19 | 2021-08-06 | 福马治疗股份有限公司 | 活化丙酮酸激酶r |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997045419A1 (en) | 1996-05-29 | 1997-12-04 | Warner-Lambert Company | Benzoxazinone dopamine d4 receptor antagonists |
| EP0900792B1 (en) * | 1997-09-02 | 2003-10-29 | Duphar International Research B.V | Piperazine and piperidine derivatives as 5-HT1A and dopamine D2-receptor (ant)agonists |
| TW546299B (en) | 1999-01-07 | 2003-08-11 | Wyeth Corp | 3,4-dihydro-2H-benzo[1,4]oxazinyl-methyl-[3-(1H-indol-3-yl)-alkyl]-amines |
| AU2494300A (en) | 1999-01-07 | 2000-07-24 | American Home Products Corporation | 3,4-dihydro-2h-benzo(1,4)oxazine derivatives |
-
2001
- 2001-10-22 DE DE60127434T patent/DE60127434T2/de not_active Expired - Fee Related
- 2001-10-22 HU HU0301458A patent/HUP0301458A2/hu unknown
- 2001-10-22 MX MXPA03003820A patent/MXPA03003820A/es unknown
- 2001-10-22 EP EP01988720A patent/EP1330460B1/en not_active Expired - Lifetime
- 2001-10-22 BR BR0114881-8A patent/BR0114881A/pt not_active IP Right Cessation
- 2001-10-22 WO PCT/EP2001/012344 patent/WO2002034754A2/en active IP Right Grant
- 2001-10-22 CN CNA018197663A patent/CN1478092A/zh active Pending
- 2001-10-22 AT AT01988720T patent/ATE357448T1/de not_active IP Right Cessation
- 2001-10-22 CA CA002426706A patent/CA2426706A1/en not_active Abandoned
- 2001-10-22 CZ CZ20031163A patent/CZ20031163A3/cs unknown
- 2001-10-22 JP JP2002537744A patent/JP4242643B2/ja not_active Expired - Fee Related
- 2001-10-22 AU AU2002224791A patent/AU2002224791A1/en not_active Abandoned
- 2001-10-22 ES ES01988720T patent/ES2280417T3/es not_active Expired - Lifetime
- 2001-10-22 KR KR10-2003-7005789A patent/KR20030051747A/ko not_active Application Discontinuation
- 2001-10-22 PL PL01366378A patent/PL366378A1/xx not_active Application Discontinuation
- 2001-10-22 US US10/415,119 patent/US6939871B2/en not_active Expired - Fee Related
- 2001-10-22 IL IL15552001A patent/IL155520A0/xx unknown
- 2001-10-24 TW TW090126222A patent/TWI237023B/zh not_active IP Right Cessation
- 2001-10-24 AR ARP010104975A patent/AR034174A1/es not_active Application Discontinuation
-
2003
- 2003-04-24 NO NO20031838A patent/NO20031838L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA03003820A (es) | 2003-07-28 |
| AU2002224791A1 (en) | 2002-05-06 |
| DE60127434T2 (de) | 2007-11-29 |
| CZ20031163A3 (cs) | 2004-04-14 |
| PL366378A1 (en) | 2005-01-24 |
| AR034174A1 (es) | 2004-02-04 |
| EP1330460B1 (en) | 2007-03-21 |
| EP1330460A2 (en) | 2003-07-30 |
| IL155520A0 (en) | 2003-11-23 |
| NO20031838L (no) | 2003-06-24 |
| JP4242643B2 (ja) | 2009-03-25 |
| US20040063704A1 (en) | 2004-04-01 |
| ES2280417T3 (es) | 2007-09-16 |
| NO20031838D0 (no) | 2003-04-24 |
| WO2002034754A2 (en) | 2002-05-02 |
| KR20030051747A (ko) | 2003-06-25 |
| ATE357448T1 (de) | 2007-04-15 |
| WO2002034754A3 (en) | 2002-07-11 |
| US6939871B2 (en) | 2005-09-06 |
| TWI237023B (en) | 2005-08-01 |
| DE60127434D1 (de) | 2007-05-03 |
| HUP0301458A2 (hu) | 2003-10-28 |
| JP2004516250A (ja) | 2004-06-03 |
| BR0114881A (pt) | 2003-09-30 |
| CA2426706A1 (en) | 2002-05-02 |
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